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【结 构 式】 
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【药物名称】 【化学名称】2-(4-tert-Butyl-2,6-dimethylbenzyl)-1,4,5,6-tetrahydropyrimidine 【CA登记号】246544-20-7, 246544-18-3 (hydrochloride) 【 分 子 式 】C17H26N2 【 分 子 量 】258.41017 |
【开发单位】NPS Allelix (Originator), Virginia Commonwealth University (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Antimigraine Drugs, 5-HT1D Agonists |
合成路线1
Alkylation of sodium cyanide with 4-tert-butyl-2,6-dimethylbenzyl chloride (I) afforded nitrile (II). Imidate (III) was then prepared by Pinner reaction of nitrile (II) with ethanolic HCl. Cyclization of (III) with 1,3-diaminopropane (IV) in ethanol furnished the desired cyclic amidine. In an alternative procedure, the target amidine was directly obtained by melting at 200 C nitrile (II) with the mono-tosylate salt of 1,3-diaminopropane.
| 【1】 Prisinzano, T.; et al.; Imidazoline-modified benzylimidazolines as h5-HT1D/1B serotonergic ligands. Bioorg Med Chem 2001, 9, 3, 613. |
| 【2】 Glennon, R.A.; Law, H. (NPS Allelix Corp.; Virginia Commonwealth University); Imidazoles with serotonin receptor binding activity. US 5969137; WO 9812183 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 49759 | 5-(tert-butyl)-2-(chloromethyl)-1,3-dimethylbenzene | C13H19Cl | 详情 | 详情 | |
| (II) | 49760 | 2-[4-(tert-butyl)-2,6-dimethylphenyl]acetonitrile | C14H19N | 详情 | 详情 | |
| (III) | 49761 | ethyl 2-[4-(tert-butyl)-2,6-dimethylphenyl]ethanimidoate | C16H25NO | 详情 | 详情 | |
| (IV) | 19331 | 3-aminopropylamine; 1,3-propanediamine | 109-76-2 | C3H10N2 | 详情 | 详情 |